Triethylamine → HCID 56847871, compound

Participants

Reaction Steps

To a stirred yellow solution of VII (290.8 mg, 0.852 mmol) in anhydrous THF (10 mL) was added 1-dodecylamine (174 mg, 1.1×0.852 mmol) and then, dropwise, triethylamine (118 mg, 132 μL, 1.1×0.852 mmol). The solution was stirred for 3.5 hours at room temperature. The colorless solution was then diluted with diethylether and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (6:4, v/v) to give 165 mg (48%) of a white solid, 10: mp=54-56° C. (uncorrected); Rf=0.61 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8.0 Hz, 1H), 6.95 (d, 4J=1.55 Hz, 1H), 6.92 (bd, 3J=8.0 Hz, 1H), 5.04 (s, 2H), 4.69 (bs, 1H; NH), 3.82 (s, 3H), 3.17 (apparent quartet, 3J=6.7 Hz, 2H), 2.29 (s, 3H), 1.51-1.43 (m, 2H), 1.32-1.19 (m, 18H), and 0.86 (t, 3J=7 Hz, 3H). Exact mass (FAB+) calculated for C23H38NO5 [M+H] 408.2744. found 408.2749.

Provenance & Evidence